MedKoo Cat#: 317626 | Name: Diphenylpyraline
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diphenylpyraline is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class.

Chemical Structure

Diphenylpyraline
Diphenylpyraline
CAS#147-20-6 (free base)

Theoretical Analysis

MedKoo Cat#: 317626

Name: Diphenylpyraline

CAS#: 147-20-6 (free base)

Chemical Formula: C19H23NO

Exact Mass: 281.1780

Molecular Weight: 281.40

Elemental Analysis: C, 81.10; H, 8.24; N, 4.98; O, 5.69

Price and Availability

Size Price Availability Quantity
100mg USD 285.00 2 weeks
250mg USD 500.00 2 weeks
500mg USD 850.00 2 weeks
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Synonym
Diphenylpyraline; Dayfen; Difenilpiralina; Diphenylpyrilene; DPP; AN 1041; AN-1041; AN1041;
IUPAC/Chemical Name
4-(benzhydryloxy)-1-methylpiperidine
InChi Key
OWQUZNMMYNAXSL-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3
SMILES Code
CN1CCC(OC(C2=CC=CC=C2)C3=CC=CC=C3)CC1
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Diphenylpyraline is a potent histamine H1 receptor antagonist.
In vitro activity:
TBD
In vivo activity:
Maximal dopamine uptake inhibition was observed 40 min after DPP (diphenylpyraline) and 30 min after cocaine administration. Post hoc tests revealed that DPP exhibited a prolonged effect on dopamine uptake inhibition in comparison to cocaine. DPP treated mice showed a significantly higher apparent Km after 40 (t=3.275; P<0.01), 50 (t=4.473; P<0.01) and 60 (t=4.699; P<0.01) min in comparison to cocaine treated mice. Reference: Eur J Pharmacol. 2012 May 15;683(1-3):161-5. https://pubmed.ncbi.nlm.nih.gov/22445882/
Solvent mg/mL mM
Solubility
DMF 30.0 106.61
DMSO 65.0 230.99
Ethanol 30.0 106.61
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.78
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 281.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Oleson EB, Ferris MJ, España RA, Harp J, Jones SR. Effects of the histamine H₁ receptor antagonist and benztropine analog diphenylpyraline on dopamine uptake, locomotion and reward. Eur J Pharmacol. 2012 May 15;683(1-3):161-5. doi: 10.1016/j.ejphar.2012.03.003. Epub 2012 Mar 15. PMID: 22445882; PMCID: PMC3340496. 2. Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR. Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. doi: 10.1016/j.ejphar.2004.11.017. Epub 2004 Dec 8. PMID: 15627433.
In vitro protocol:
TBD
In vivo protocol:
1. Oleson EB, Ferris MJ, España RA, Harp J, Jones SR. Effects of the histamine H₁ receptor antagonist and benztropine analog diphenylpyraline on dopamine uptake, locomotion and reward. Eur J Pharmacol. 2012 May 15;683(1-3):161-5. doi: 10.1016/j.ejphar.2012.03.003. Epub 2012 Mar 15. PMID: 22445882; PMCID: PMC3340496. 2. Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR. Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. doi: 10.1016/j.ejphar.2004.11.017. Epub 2004 Dec 8. PMID: 15627433.
1: Oleson EB, Ferris MJ, España RA, Harp J, Jones SR. Effects of the histamine H₁ receptor antagonist and benztropine analog diphenylpyraline on dopamine uptake, locomotion and reward. Eur J Pharmacol. 2012 May 15;683(1-3):161-5. doi: 10.1016/j.ejphar.2012.03.003. Epub 2012 Mar 15. PubMed PMID: 22445882; PubMed Central PMCID: PMC3340496. 2: Montijo-Barrios E, Cadena F, Ramírez-Mayans JA, Gutiérrez-Castrellón P. [Clinical trial on the effect of buphenine, aminophenazone and diphenylpyraline hydrochloride in treating the common cold in children of 6 to 24 months of age]. Rev Invest Clin. 2011 Jul-Aug;63(4):335-43. Spanish. PubMed PMID: 22364032. 3: Weis R, Faist J, di Vora U, Schweiger K, Brandner B, Kungl AJ, Seebacher W. Antimycobacterial activity of diphenylpyraline derivatives. Eur J Med Chem. 2008 Apr;43(4):872-9. Epub 2007 Jul 10. PubMed PMID: 17714832. 4: Shakleya DM, Jansson LM, Huestis MA. Validation of a LC-APCI-MS/MS method for quantification of methadone, 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine (EDDP) and 2-ethyl-5-methyl-3,3-diphenylpyraline (EMDP) in infant plasma following protein precipitation. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Sep 1;856(1-2):267-72. Epub 2007 Jun 16. PubMed PMID: 17602899. 5: Choo RE, Murphy CM, Jones HE, Huestis MA. Determination of methadone, 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, 2-ethyl-5-methyl-3,3-diphenylpyraline and methadol in meconium by liquid chromatography atmospheric pressure chemical ionization tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jan 25;814(2):369-73. PubMed PMID: 15639461. 6: Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR. Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. PubMed PMID: 15627433. 7: Puhakka H, Rantanen T, Virolainen E. Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41. PubMed PMID: 14039. 8: KNOCHE C, KOENIG J. [ON THE PRENATAL TOXICITY OF DIPHENYLPYRALINE 8-CHLOROTHEOPHYLLINATE WITH REFERENCE TO EXPERIENCES WITH THALIDOMIDE AND CAFFEINE]. Arzneimittelforschung. 1964 May;14:415-24. German. PubMed PMID: 14238604. 9: ANDRE J, EILARD U, HELLGREN L. [Diphenylpyraline HCl (Histyn) in long-acting preparations (Durettes) in hay fever]. Sven Lakartidn. 1961 Apr 28;58:1245-9. Swedish. PubMed PMID: 13683344. 10: HELFAND AE. Clinical evaluation of "diphenylpyraline" as an antifungal agent in tinea pedis. A preliminary report. J Am Podiatry Assoc. 1961 Feb;51:109-11. PubMed PMID: 13713076. 11: NACHTIGALL HB. Clinical evaluation of diphenylpyraline. J Allergy. 1956 Jan;27(1):75-7. PubMed PMID: 13294977. 12: VAN DE ERVE J Jr. Fungicidal activity of diphenylpyraline. AMA Arch Derm Syphilol. 1953 Nov;68(5):572-4. PubMed PMID: 13091417. 13: Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I. Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7. PubMed PMID: 11137513. 14: Vasudevan M, Ravisankar S, Sathiyanarayanan A, Chandan RS. Simultaneous estimation of phenylpropanolamine HCl, guaiphenesin and diphenylpyraline HCl in syrups by LC. J Pharm Biomed Anal. 2000 Dec;24(1):25-31. PubMed PMID: 11108536. 15: Ebete KO, Koundourellis JE. Determination of diphenylpyraline in plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Mar 3;677(2):319-23. PubMed PMID: 8704936. 16: de Fabrizio F. GLC analysis of theophylline, hydroxyethyltheophylline, and diphenylpyraline hydrochloride syrup. J Pharm Sci. 1979 Apr;68(4):521-2. PubMed PMID: 35600. 17: Graham G, Bolt AG. Half-life of diphenylpyraline in man. J Pharmacokinet Biopharm. 1974 Jun;2(3):191-5. PubMed PMID: 4156058. 18: Kuokkanen K, Paavilainen O. Evaluation of slow-releasing diphenylpyraline in chronic urticaria and various kinds of dermatites. Acta Allergol. 1971 Dec;26(6):454-62. PubMed PMID: 4401352. 19: PADBERG G. [BIOCHEMICAL STUDIES ON THE MATURATION OF FETAL CONNECTIVE TISSUE UNDER THE INFLUENCE OF DIPHENYLPYRALINE-8-CHLOROTHEOPHYLLINATE AND CAFFEINE]. Arzneimittelforschung. 1964 May;14:424-8. German. PubMed PMID: 14238605. 20: FARRERONS-CO J. [Present status of antihistamine therapy. Clinical evaluation of diphenylpyraline]. Med Clin (Barc). 1962 Nov;39:346-50. Spanish. PubMed PMID: 13944461.